.When my father went to bed later Sunday evening he wore a pair of Mom’s panties – the pair she’d used to stroke his cock earlier that evening.
Mom had never seen Dad come to bed wearing her panties before and found his deeper lingerie fetish good news. Years ago she caught him whacking off into a pair of her dirty panties, and she had incorporated panty-fapping into their regular routine. Many was the night my dad was more eager for intercourse than Mom was, and this was a simple way for her to get him done so she could sleep.
To speed things up even more, she would normally tell him over and over again that his cock was too small to please her vagina and that of the few men she’d ever fucked, his was tiniest. It didn’t matter whether this was exactly true or not; Mom’s verbal degradation stoked Dad’s lust.
Nevertheless, coming to bed wearing cum-soaked panties was a first, and since he hadn’t said anything about it, neither did Mom.
Monday night he came to bed wearing panties again. This time she shot him a look with a raised eyebrow that asked, without words, what was going on.
“I’ve decided I like the fit of panties,” Dad said. “I sleep better without my junk moving around as much when I toss and turn. They’re tighter and hug my balls and penis nice and snug. It doesn’t mean anything sexual.”
But by Thursday morning, Dad was going to the office sporting a pair of panties under his boxers. When Mom noticed this Friday morning, she asked what he was up to. Dad hemmed and hawed a bit, and explained that the panties were so comfortable, especially when he sat in a chair most of the day. He told Mom that most women had no idea how uncomfortable sitting down for hours is for a man. He’s basically crushing his own testicles all day! But he had to hide them under the boxers in case anyone saw him, say at the urinals.
Mom heard him out and didn’t argue. She told him women feel the same way about their breasts sometimes – boobs move around uncontrollably and sometimes bump into things. Many women wear sports bras because they feel better with their tits strapped down.
Like most teenagers, I’d drawn away emotionally from my parents when I got old enough to drive. So I was a little surprised Friday at dinner when Dad asked me if I could come along with his golf foursome on Saturday. I didn’t play golf, but Dad said it would be fun for me to drive the golf cart and he’d like to spend more time with me and not feel guilty when he spent hours on the course.
Jake had asked me early in the week if I wanted to go cruise for girls again Friday night. I knew what Jake had in mind, of course, but now that his cousins’ vacation was over I felt safe going for a ride with only Jake in the car.
Before the holiday, and the wild events that took place, he and I had regularly gone out on Friday and Saturday nights to drive around, hit a few of the teenage hangouts, and then park the car in a remote spot to have sex. Well, I guess Jake had all the sex – I just blew him every night and went home with the delicious taste of his jizz in my mouth.
At first, Jake had offered to reciprocate, but we both soon realized that I would always decline the offer. I’d grown to adore the powerful feeling of making Jake come erect in my mouth, and then drawing his seed from deep down in his balls. He felt dominant because he was the one with his dick in a hole, but I felt powerful because I decided when and where he would come. Which was usually “ASAP,” and “in my thirsty, sucking mouth.”
A lot had happened to both of us during that two-week vacation, and neither of us knew what the other had done. I had no idea that Jake had fucked my mother senseless the weekend before, and Jake didn’t know that my Mom had jerked me off into her panties and blown me in front of my Dad.
So, late Friday night found me parked in a dark spot with Jake. “Let’s get in the back seat,” I offered. I’d blown Jake in the front seat several times, and if we made room on the floor I was able to kneel under the dashboard and suck him while he stayed in the driver’s seat. But once we experienced the relative comfort of the back seat, we preferred it. The front seat was “safer.” If another car approached us, as had happened twice, we could pretty quickly look presentable for an unwanted audience. Two guys caught in the back seat would be pretty obvious.
As I stretched out lengthwise in the back seat, I remembered clearly how thoroughly Jake and his cousin John had fucked me senseless in that seat almost 2 weeks before. One cock in my mouth, one in my ass, switching back and forth until we were all exhausted. Both of the guys, but mostly John, telling me the whole time that I was a fag and a sissy to let other guys cum in me. I’d felt so dirty and used. I thought, in my ignorance, that I was a freak, that no other boy would ever welcome the sexual degradation that I seemed to love.
Yet someday, I knew, I would want that feeling again. I was young, only 18, but already knew that more dick is better than less. John’s fatter, uncut cock had been a delight to suck. That it was slightly plumper and meatier than Jake’s dick had made the sensations even better when it plunged in and out of my ass.
I wondered fleetingly if Jake would be willing to share me again. Who could we get? I can’t just go to class and ask random guys to have gay group sex. But the vague thought of another threesome made me tingle with excitement.
And what would four or five guys be like, I asked myself? Being humiliated for sucking cock somehow made the cum taste better. Jake could do and say a lot of things to give me the humiliation I seemed to need. But is there *anything* more degrading that one man can do to another than to cum in him and then say to a third guy “Here, you fuck his sloppy hole now?”
Although there was no need for me to undress to suck him off, or even for him to undress, Jake suggested we take our pants off as we got comfortable in the rear seat. I rearranged myself prone so that I was face down on the seat, my mouth tightly attached to Jake’s groin. Miraculously, as I hunched my groin into the seat cushion and remembered my three-way with the guys, my little penis got stiff as a board.
I’d actually missed his cock in my mouth and was energetically bobbing my head up and down when he started to finger my ass. Our positions made it easy for him to lean slightly with an outstretched arm and finger my anus. A few moments later his finger was lubed and penetrating me easily. (Sneaky fucker. Where had he hidden the lube?)
Long before Jake was ready to orgasm he said “Are you ready to be ‘my girlfriend’ again? I love it when you suck me, but I really need to fuck ‘Donna’ again.”
I loved being “Donna” for Jake and didn’t need any arm-twisting. I got up on hands and knees and faced away from “my boyfriend.” Thanks to the lube and the loosening by Jake’s fingers, he hilted his hot, thin, saliva-slicked erection into my “pussy” smoothly, in one exquisitely slow thrust.
The sensation was fantastic. While Jake’s cock was noticeably bigger than mine, he wasn’t some freak of nature. In fact, his cousin’s cock was bigger yet, and John had taken my ass nicely several times during his visit. My rectum liked the feeling of being stuffed full of another guy’s dick. As long as Jake moved in and out very slowly, and with adequate lube, it was a delicious sensation.
Even my sphincter felt pleasure. When the well-lubed knob of Jake’s meatloaf slowly popped it open, the muscle would try to snap tight around the crown of his dick like it wanted to hold him in place, shaft yet to come. Then, when Jake slowly withdrew, his glans would force my anus open just a little bit more, and then let my asshole slam shut upon withdrawal. Somehow 50% of the joy of anal sex came from the first inch of hard dick. The other half was prostate. As long as a guy’s cock was long enough to bang my gland, it was enough cock to get me off.
We were both moaning our pleasure as the windows fogged up. I came first, shooting my load hands-free onto the rear seat. Jake proudly announced: “I fucked the cum out of you, didn’t I Donna?” which made sense only to us. I was Donna for him, but I had a cock, and he could fuck the cum out of his “girlfriend.” Hands-free orgasms, my swaying cock-shaft pumping sperm into mid-air, my balls aching just before release, those were the *best* orgasms.
Jake ordered me to lick up my mess, and I was ass up, face down, tongue busy lapping spunk off the car seat when Jake’s wonderful delicious dick exploded in my ass-pussy.
As we cleaned up and got dressed, Jake asked me about a repeat Saturday night. I told him I doubted I’d be up for it because I’d be on the golf course with my Dad all afternoon. A golf outing for my Dad usually took 5 or 6 hours.
I expected Jake to be disappointed, but he didn’t seem to mind the prospect of a night without sex. Maybe I’d exhausted my boyfriend, I thought, and smiled. Jake asked me for details about where we’d be golfing, and what times. It never occurred to me that Jake had an ulterior motive for his interest about who in my family would be where, when, on Saturday.
Dad and I were only 15 minutes gone when Jake phoned my Mom. Soon after that, he arrived at our house. When Jake phoned, Mom had thought briefly about denying him. But she knew Jake had all the leverage, all the power in their twisted relationship. So instead of making an excuse when Jake phoned, the last thing she said to him was “I can’t wait for that wonderful thing you do with your tongue. You know, back there.”
Her first encounter with Jake, the weekend before, had been full of threats and accusations, shouted arguments about who would report whom to the Police, or release incriminating videos or audios of what, where. Their ensuing sex acrobatics were angry and lacking tenderness, even hostile. “Hate-fucking,” it’s called.
It ended enjoyably for Mom, but she felt like she’d been coerced, that something had been taken from her. Despite my mother’s calm middle-aged demeanor, she was not somebody to piss off. Mom somehow craved Jake’s cock and disliked him intensely at the same time. Even when Jake was giving Mom maximum pleasure, tossing her salad, she harbored quiet resentment towards him for fucking me so many times, for pumping so much of his sperm into her baby boy’s asshole.
And underneath all her other attitudes about Jake, repressed to a depth that made her only dimly aware it was there, was the perverted sense that she was competing sexually against her own son for this talented penis and the young man to whom it was attached.
When my mother sucked Jake’s dick, it was with a tiny doubt about which one of us sucked him better. Mom loved anal sex now that the final reward was Jake cleaning out her spermy anus, but could her middle-aged ass possibly be as tight as an 18-year-old boy’s?
Today Mom did everything because *she* wanted to, and whatever Jake took last week, she took back twice as much this week. About the time Dad was teeing off on the first hole, Jake was stuffing that delicious cock of his, the one I loved to suck, into my mother’s dripping wet cunt-hole. It was no monster, just really on the long side of *average*, but it was the biggest cock Mom had to work with, and she got right to work.
Jake was smart enough to know that his “signature move,” eating my mother’s ass, was his all-access pass for the rest of today and forever. After giving Mom her first orgasm, he slid his hard cock from her cunt to her asshole and slithered in slowly. Soon, after loading her rectum with his first, therefore copious, ejaculation, he spent almost 15 minutes gently making love to her stretched and sore anus, even making a poorly focused vid of himself lapping up her rectal creampie.
With at least four hours of privacy, my MILF mother and her high school lover tried a little of everything. Jake took more pictures and vids that day, of his cock in Mom’s ass, cunt, and mouth. He made her pose. A large part of his pleasure came from insulting and degrading the middle-aged slut who he had at his mercy. He gleefully kept referring to her as “Mrs. Thompson” and “Donny’s whore mother.” She loved it and even joined in. “You don’t have enough cock for your buddy’s nasty momma, do you, little man?”
With phone in hand (or filming from a nearby tabletop), Jake made his own porn video out of my Mother’s sexual degradation. The dialogue was straight from all the cheesy porn movies he’d ever seen, stuff about Mom’s uncontrollable lust for cock and her worthless, sissy husband. You’ve seen on-line porn vids, too, I’ll bet, so know what kinds of things Jake babbled to humiliate Mom.
And for every insulting remark, Mom had one in response. At one point he gave her a lame facial, his balls being mostly drained by then, and as he squirted she mocked “Is that the best you can do?”
At another point, she struck a chord when she moaned “I wonder who’s fucking *your* mother while you’re fucking me?” Jake shivered as he imagined, for the first time, his mother having sex with someone other than his father; her legs wrapped around one of his classmates perhaps.
After two satisfying hours, Jake left our house long before Dad and I were due back. He left my mother sore, crusty with half-dry body fluids, and exhausted. She’d never been happier.
Most of the way home he thought not of my mother naked and spread-eagled, but his own. Mom had really played with his head.
When Dad and I got home, Mom was in the shower. Dad and I went to our rooms and to wash up for dinner. We’d brought in some pizza so Mom wouldn’t have to cook. I took a quick shower to wash the gnats and grass clipping off of myself, and Dad tried to jump into the shower with Mom. He was trying to get frisky, but she shot him down and said they could “play after dinner.”
Most Saturdays Dad washed the dishes. It was a way to pay Mom back for letting him abandon his family for most of every Saturday. Mom and I left him to it, and after channel surfing the news programs, my mother turned to me and told me she wanted to play with her “undies and bras” again tonight like we three had done last week. I was thrilled, of course, and without saying anything to Dad she led me down the hall to their bedroom.
Once there, no mention was made of Dad or her plans for him to join us. I just assumed he would. Mom directed me to stand quietly while she pulled out many of her ladies’ undergarments. She held up one brassiere in front of me and said “this one. Strip.”.
So I did. I took off my shirt and trousers, but when I hesitated to remove my underpants, Mom just pulled them off herself. She knelt in front of me, tugged them over my hips, and stayed on her knees, face inches from my groin. I wasn’t even half-hard yet. I was still not sure what we were going to do, what with my father right there in the house with us. My mother took my cock droop as a personal insult and started to lick my dangling penis while muttering “I’ve got big plans for your cock tonight, Don.” That worked.
When she had me acceptably stiff she stood up and held out the bra in a way that made it clear to me that she would fasten it on me. So I raised my hands over my head and backed into her open arms. She made a small production out of caressing my nipples, placing the cups over my chest, and fastening the bra in the back. The simple actions stiffened my cock even more.
Before I could step forward, out of Mom’s embrace, she lowered her hands and stroked my cock gently. “It’s going to be a shame to put this away, even in a nice pair of lacy panties, isn’t it, Donna?” she hissed into my ear. I was drooling pre-cum from the head of my erection. My mother fondled my balls for a minute or two and said: “I hope you’ve got a big load in these hot nuts for Mommy and Daddy tonight.”
She released me and handed me a pair of barely-there low-rise bikini panties that matched the bra I was wearing. She quickly took them back from me, said “no, let me help you,” and went back to her knees. I held her shoulder for balance and raised first one leg, then the other, as she slowly lifted the panties towards my crotch. She seductively made a big show out of licking with her tongue up my stretched scrotum and the length of the underside of my hard-on. Just as she raised the panties into place, failing of course to contain even half of my five-inch erection, Dad came in.
“Get into your frilly things, darling. Don’s already dressed.”
Mom had always been the dominant one in their bedroom. It’s not so much that she was brassy and bossy, more that Dad was meek and mild. He’d married way out of his league somehow, and he always knew she could have hooked a better-looking man, or a more athletic one. It was like the Head Cheerleader married the head of the Chess Club.
Even in the first year or two of their marriage, Mom was starting to assert herself in their bedroom. Dad’s penis was just barely average, five inches hard and not very thick. Mom’s orgasms usually required that Dad perform oral sex before and after their intercourse. He had balked, at first, about the “after” part, but Mom just climbed on his face and forced her crotch over his mouth. “Aren’t you glad now that you don’t cum very much, Darling,” she taunted him.
So when Mom told Dad that night to get into his feminine underwear, he didn’t even hesitate to do as she told him.
I studied his naked body before he put on his negligee. He was an inch taller than me, but maybe 30 pounds heavier. He wasn’t fat, but he was pale, soft, even pudgy. I noticed for the first time, as he put on his brassiere, that he had just a hint of manboob to go into the cups. His torso was hairless except for some fine hairs on his legs, and under his arms.
His dick was erect and could have been a carbon copy of mine. We are both circumcised, and our thin shafts make the heads of our dicks look bigger than they actually are. How could he satisfy a sex bomb like Mom with that little cock? More importantly, how would *I* ever keep a real woman satisfied? Dad and I together maybe made one cock in total.
Now Mom told us to lie crosswise on the large bed, side by side, on our backs. I was closest and got to the bed first. As Dad approached, I reached up to hesitantly caress his erect cock, snug in his panties, throbbing inches in front of me. I wasn’t sure how my touch would be received. I only had Jake’s and John’s to compare Dad to, and his organ was the smallest of all of us. He moaned as I fondled his hairless balls, and I bent over to place a quick kiss on the protruding head of the dick that had made me.
We took our places on the bed as directed by Mom. Both our heads pointed towards the door and our feet towards the far wall. My mother stood now between our heads, facing our feet, and leaned forward to caress our panty-clad cocks.
I turned my head to look at Dad, but Mom’s hips blocked us. He reached up with one hand and stroked Mom’s ass under her skirt. I was tempted to join him but didn’t. So far, Mom had been in my driver’s seat. She told me what to wear, and what to do. I was comfortable letting her decided what touched who, where. I kept my hands at my sides and enjoyed the sensation of my mother kneading my cock and balls through my silky panties, gripping me and stroking my penis.
But as she bent over me, I desperately wanted to suckle again at her tits. “Mom, please, take off the top so I can kiss your breasts.”
Mom didn’t hesitate at all before standing erect, shucking her polo, and unsnapping her bra. She returned to her bent over position and dragged her nipples across my mouth. My lips went crazy trying to snare her nipples. My mother had the most beautiful tits I could imagine. They were full, and natural, of course. They drooped only slightly, but her aureoles and nipples pointed straight ahead, not downwards.
To hold herself in position, halfway bent over, keeping her beautiful boobs over my face, she re-positioned her hands from our two crotches to my hips. She held me firmly in position and braced herself at the same time. This made it easier for Mom to keep tormenting me with her hard, rigid nipples. I loved this part, nursing at my mother’s breasts as I did 18 years before.
I prepared to fondle my own now-neglected dick but now felt two other hands peeling down my panties. It was my father, of course, gently exposing my sex organs. As Mom kept swaying, blocking my view, I choked “Mom, Dad, Mom,” and stopped mid-sentence because I had no idea what I could say.
I couldn’t see what my father was doing, but as I raised my hips off the bed to make stripping me easier, Mom spoke: “That’s right, Bill, take your son’s cock out. Isn’t it beautiful? It’s exactly like yours. But maybe a little bit bigger? They’re *all* a little bit bigger, aren’t they, Bill?” Mom taunted.
I felt Dad grab the root of my dick and pull it towards him.
“Is that why my big boy never showers at the club after golf? Does a shower room full of bigger cocks make Billy intimidated? Maybe a little curious?”
Then I felt a tongue lapping my ball sack.
“It’s OK to suck him, Daddy. Suck his little hard-on. You want Don’s cock, don’t you darling? Drink your son’s cum-load?”
I thought my head would explode from the bizarre perversity of what was happening. My father’s mouth now pulled at my erect penis like a vacuum machine. One of his hands held my cock firmly so that I couldn’t move, and Dad’s other hand fondled my balls so that I didn’t want to.
Meanwhile, Mom continued to hold me in place by my hips, maybe so I could keep nursing, but maybe so that my father could drain my balls into his mouth. Bent over us, she could see who was doing what and encouraged us with her soft voice. “Is this the first cock you ever sucked, Bill?”
With my cock in his mouth, he couldn’t answer Mom. I thought probably not. I’d spent several hours by now with either Jake or John’s dicks pillaging my throat, and I knew the difference between a clumsy fumble and a first-rate testicle drain. My father was a top-notch sucker of dick. Maybe sometimes he *did* visit the locker room…
My hand was able to touch, and stroke, Dad’s back. He was still wearing Mom’s bra and panties, and I softly stroked them both. Mom said “Rub his ass. It’s like a woman’s ass, isn’t it? Pretend it’s my ass, baby. Pretend it’s your mommy sucking your beautiful cock, not your sissy daddy.”
Dad responded to my caresses and Mom’s muttering by tugging with his hands and pulling with his lips as I got closer to my release. My hand now snaked inside his lacy panties, and I gently caressed Dad’s bare hairless butt cheeks.
I thought about what I liked done to me, and got my fingertips under the material of the panties to touch his puckered anus. My finger was dry, and wouldn’t penetrate his tightly-clenched barrier. I didn’t want to hurt him, so I pulled back.
“Don, let Mommy do it.” While her husband sucked furiously at my erect cock she reached into the nightstand and retrieved the KY. She slathered lube generously at his back door. “I can’t do this with my long fingernails, Donny. You go inside.”
And, for the first time in his life, another man’s finger gently entered Dad’s asshole. As I slid it as deep as I could, Dad’s mouth came off of my cock and he barked his release, ejaculating all over my leg and the bed. Slowly he slumped back over my crotch, but he was too depleted to continue sucking my dick.
“Oh, Bill, do I have to do everything for you?” Mom said and took me between her luscious lips. I thought my balls were going to come out of my urethra as I had a colossal orgasm into my Mommy’s mouth.
When I opened my eyes, Mom was still extended over me, tits over my chin and her face over my groin next to Dad’s head. Once again she snowballed my large load into her husband’s accepting mouth. Their French kiss, while their heads were inches above my empty balls, Mom’s hair tickling my shrinking dick, lasted a long time.
“Thank you, darling,” Mom whispered to Dad. “You’re always going to be my first boy, you know that, don’t you? You’re not much of a man, but you’re Mommy’s very good boy.”
Dad just nodded, peaceful and drained. He had resumed nibbling the head of my cock.
“My first little boy always does what Mommy asks, doesn’t he?”
I felt his head bob as he gave my mother another silent nod.
I lay there peacefully myself, pondering my new title “second boy.” It was kind of cute. I wondered what dirty plans Mom was turning over in her head for her “boys.”
Only a month before I’d thought of this woman as an almost sexless old lady. Now I saw my Mom as the horniest cunt in town. She was twisting men into boys and boys into girls and my father and I were just her pawns. My mind wandered further. Neither Dad nor I got anywhere near Mom’s pussy when we played. Was Mom gay; didn’t she want cock?
The undersides of Mom’s breasts were in front of my face. Her flesh was covered by at least six large blue bruises. Not knowing what I was doing, I blurted out “Geez Mom, who gave you all those hickeys on your boobs?”